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Enzymatic Synthesis of 1-Sinapoylglucose from Free

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Enzymatic Synthesis of 1-Sinapoylglucose from Free Enzymatic Synthesis of 1-Sinapoylglucose from Free Sinapic Acid and UDP-Glucose by a Cell-Free System from Raphanus sativus Seedlings Dieter Strack Botanisches Institut der Universität zu Köln, Gyrhofstr. 15, D-5000 Köln 41 Z. Naturforsch. 35 c, 204-208 (1980); received December 28, 1979 Raphanus, Brassicaceae, Phenylpropanoid Metabolism, Glucose Ester, Esterification. Protein extracts from seedlings of Raphanus sativus catalyze the transfer of the glucosyl moiety of UDP-glucose to the carboxyl group of phenolic acids. Enzymatic activity was determined spec- trophotometrically by measuring the increase in absorbance at 360 nm and/or by the aid of high performance liquid chromatography (HPLC). From 12 phenolic acids tested as acceptors, sinapic acid was by far the best substrate. The glu- cosyltransfer to sinapic acid has a pH optimum near 7 and requires as SH group for activity, p- Chloromercuribenzoate (PCMB) inhibits activity, which can be restored by the addition of di- thiothreitol (DTT). The formation of 1-sinapoylglucose was found to be a reversible reaction, sin­ ce the addition of UDP results in a breakdown of the ester. Introduction Materials and Methods Higher plants contain a large number of various Plant material and culture conditions are described hydroxycinnamoyl esters. Most of them might be elsewhere [10]. synthesized via hydroxycinnamoyl-CoA thiolesters as the activated reaction partners [1]. The widely Thin-layer chromatography occurring glucose esters [2], however, might be Phenolic acid derivatives were chromatographed exclusively synthesized from free hydroxycinnamic on microcrystalline cellulose (Avicel) in CAW, chlo­ acids and UDP-glucose [3, 4]. The formation of roform - acetic acid - water (3 : 2, water saturated) glucose esters of benzoic acids might follow the same and were detected under UV with and without NH3- mechanism [5], vapor. Sugar chromatography was carried out on Whereas the involvement of UDP-glucose is well the same layer with BPW, w-butanol — pyridine — established in the formation of phenylpropanoid water (3:1:1) with an overflow technique: The glycosides, containing hydroxycinnamyl alcohols [6], upper margin of the plates was connected with chro­ flavonols [7, 8], or anthocyanidins as aglyca [9], there matographic paper, which hung over the back of the is a lack of knowledge of the enzymatic reaction of plates and allowed development for 15 —20 h. Sugar glucose ester formation. detection was achieved with ammoniacal silver ni­ Seedlings of Raphanus sativus accumulate a high trate [11]. amount of 1-sinapoylglucose (80—100 nmols per cotyledon) in early stages of germination. The sinapic High performance liquid chromatography acid of this ester is derived from sinapoylcholine (sinapine), which is hydrolyzed by a specific sinapine The liquid chromatograph used was obtained esterase [10], from Spectra Physics (Santa Clara, Cal., USA) and The present report describes the enzymatic forma­ is described elsewhere [12]. tion of 1-sinapoylglucose via uridine diphosphate-D- The applied column (250 x 4 mm) was prepacked glucose (UDPG) and free acid by protein extracts with LiChrosorb RP-8 (5 |im) (Merck, Darmstadt, from young seedlings of Raphanus sativus. This reac­ Germany). Separations were accomplished by gradi­ tion is freely reversible, which might be of physio­ ent elution: in 35 min linear from 1% phosphoric logical significance for the Raphanus seedling. acid (A) to 70% methanol (B) in A + B. The flow- rate was 1 ml/min and detection at 330 or 265 nm Reprint requests to Dr. D. Strack. was achieved with a Schoeffel SF 770 UV-VIS 0341-0382/80/0300-0204 $01.00/0 detector (Kratos Inc., Trappenkamp, Germany). D. Strack • Enzymatic Synthesis of 1-Sinapoylglucose from Free Sinapic Acid 205 HPL-radiochromatograms from enzyme assays (1 n NaOH, room temperature for 30 min) and by containing UDP-[3H]glucose were obtained by frac­ analysis of the sugar [13], tionating eluants into 1 ml samples, which were col­ Tentative identification of glucose esters of other lected at the detector flow-cell outlet into 5 ml phenolic acids were done by HPLC and mild alka­ Unisolve I (Zinsser) in scintillation vials. Counting line hydrolysis. was done with a Tricarb-liquid-spectrometer (Pack­ ard). Results Substrates Identification of reaction products Phenolic acids were purchased from Fluka, Neu- In the presence of UDP-glucose protein extracts of Ulm, Merck, Darmstadt, and Roth, Karlsruhe. Raphanus sativus cotyledons are capable to form Uridine diphosphate-D-glucose (UDPG) disodium glucose esters with various phenolic acids (Table I). salt was obtained from Merck; UDP-D-[6-3H]glucose In each assay only one product was found (TLC, ammonium salt (3.1 Ci/mmol) from Amersham Buch- HPLC), exhibiting high sensitivity towards alkaline ler, Braunschweig; ADP, CDP, GDP, and UDP treatment. from Boehringer, Mannheim. When the enzyme assay contained sinapic acid, the product formed showed TLC and HPLC identity Preparation o f the cell-free extract with 1-sinapoylglucose, which was isolated from Raphanus sativus seedlings [13]. The sugar released To 50 seedlings 0.5 to 1.0 g insoluble Polyclar AT by alkali could not be distinguished from authentic (Serva, Heidelberg) was added and treated with an glucose. Incubations containing in addition UDP- Ultra Turrax homogenizer in an ice bath for 2 min [3H]glucose gave 1-sinapoylglucose with radioactivity in 10 ml potassium phosphate buffer (100 mM, found exclusively in the glucose moiety. HPLC pH 7.0), containing 10 mM dithiothreitol (DTT) analysis of this assay gave the expected simultaneous (Serva, Heidelberg). The suspension was centrifuged elution of the UV absorbing 1-sinapoylglucose and at 3,000 x g for 15 min, the filtered supernatant was its radioactivity (Fig. 1). HPLC analyses of incuba­ centrifuged at 38,000 x g for 30 min, and was finally tions, which contained other phenolic acids (Ta­ subjected to a Sephadex G-25 centrifugation. ble I), gave the same results. When these samples were treated with 1 N NaOH for 30 min at room Enzyme assay and determination of activity temperature the UV absorbing- and the 3H-product 100 |il protein extract was mixed with 100 jj.1 phe­ nolic acid solution (in buffer) and 2.7 ml potassium phosphate buffer (100 mM, pH 7.0, 10 mM DTT) and Table I. Specificity of the transfer of the glucosylmoiety of UDP-glucose to the carboxyl group of different phenolic preincubated for 30 min at 30 °C. The reaction was compounds. Activities were determined by calculating the started by the addition of 10 |il UDPG solution (in amount of label incorporation from UDP-[ 3H]glucose into water). Substrates were in a final concentration of each substrate, obtained by HPLC (see fig. 1). 1 mM each. Radioactive assays contained in addition Substrate (1 mM ) % Relative 3 p-Ci UDP-[6-3H]glucose. activity (compared to Enzyme activity was determined spectrophoto- sinapic acid= 1 0 0 ) metrically by measuring the increase in absorbance at 360 nm (PMQ II, Zeiss) and/or by high perfor­ Sinapic acid 1 0 0 D-Coumaric acid 40 mance liquid (radio)chromatography (Fig. 1 and 2). Ferulic acid 38 The absorbance of the produced 1-sinapoylglucose Caffeic acid 38 in the reaction mixture followed the Lambert-Beer 3,5-Dimethoxycinnamic acid 33 Cinnamic acid 16 law, which was determined by HPLC. Benzoic acid 39 Vanillic acid 36 Product identification Syringic acid 35 Anthranilic acid 31 Identification of 1-sinapoylglucose was achieved 4-Hydroxybenzoic acid 31 by TLC [13], HPLC [14], mild alkaline hydrolysis 3,5-Dihydroxybenzoic acid 5 206 D. Strack • Enzymatic Synthesis of 1-Sinapoylglucose from Free Sinapic Acid 0 10 20 30 0 10 20 30 Retention time (min) Retention time (min) Fig. 1. HPLC analyses of a protein extract from Raphanus sativus cotyledons, incubated with sinapic acid and UDP- glucose and UDP-[ 3H]glucose, (a) at t 0 and (b) after 3 h incubation. 20 nl of the incubation medium was directly injected without any pretreatment. peaks were no longer detectable. The identity of the factor of three, compared with assays without DTT. products />-coumaroyl-, feruloyl-, and caffeoylglu- 72 and 62% of this activity was obtained with 1 mM cose was further substantiated by the HPLC analysis and 100 mM DTT, respectively. PCMB at 10~3m described in ref. [14]. gave 100% inhibition, but activity could be restored up to 50% by the addition of 10 mM DTT. The Characterization of the enzymatic formation influence of 10-4 M PCMB, which inhibited to 24%, o f 1-sinapoylglucose could be neutralized by 10 mM DTT. Extraction and assay buffers with molarities be­ The amount of 1-sinapoylglucose formed from tween 50 and 100 mM potassium phosphate of pH sinapic acid and UDP-glucose was found to be values around 7.0 gave maximal activities. The addi­ proportional to added enzyme — 25 to 150^1 in tion of DTT or 2-mercaptoethanol markedly increas­ assays of 3 ml were tested - and to time up to ed the rate of sinapoylglucose synthesis. The optimal 15 min. After 3 h around 10% of the incubated free concentration of 10 mM DTT stimulated activity by a sinapic acid was converted to 1-sinapoylglucose. D. Strack ■ Enzymatic Synthesis of 1-Sinapoylglucose from Free Sinapic Acid 207 Discussion In the metabolism of plant phenolic acid esters, the central role of cinnamoyl-CoA derivatives is well established [1], However, in a few studies the in­ volvement of UDP-glucose in the formation of the most common phenolic glucose esters [3 — 5] has been demonstrated. The present report is in agree­ ment with the results of these authors and supports the assumption that this reaction might be of general occurrence for biosyntheses of phenolic glucose esters. From the fact that a wide variety of plants is able Time (hrs) to form glucose esters from fed free phenolic acids Fig.
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